Follow these detailed steps to ensure your pineapple skewers are perfectly grilled, with beautiful char marks and an irresistible caramelized glaze. The process is straightforward, but paying attention to the details will yield the best results.

1. Prepare the Glaze: In a medium-sized bowl, combine the packed light brown sugar, ground cinnamon, and the pinch of salt. Whisk them together to ensure the cinnamon and salt are evenly distributed throughout the sugar. Pour in the melted butter and the vanilla extract. Stir everything together until you have a smooth, syrupy glaze. The consistency should be thick enough to coat the back of a spoon. Set this bowl aside for now.
2. Prepare the Pineapple: If you are using wooden skewers, now is the time to place them in a shallow dish filled with water. Let them soak for at least 30 minutes. This crucial step prevents them from burning to a crisp on the hot grill.
3. Cut the Pineapple: Lay the pineapple on its side on a sturdy cutting board. Using a large, sharp chef’s knife, carefully slice off the top crown and the bottom base. Stand the pineapple upright on the flat bottom. Carefully slice downwards along the curves of the pineapple to remove the tough outer skin. Try to remove as little of the sweet flesh as possible. Once the skin is removed, you will see small brown “eyes” remaining. You can remove these with the tip of a paring knife or by making shallow, diagonal cuts to remove them in rows. Now, slice the pineapple in half from top to bottom. Lay each half flat and slice it in half again, leaving you with four long wedges. Slice off the tough, fibrous core from the inner edge of each wedge and discard it. Finally, cut the remaining pineapple flesh into uniform, 1 to 1.5-inch chunks. Uniformity is key for even grilling.
4. Marinate the Pineapple: Add all the pineapple chunks to the bowl with the brown sugar glaze. Use a spatula or your hands to gently toss the pineapple, ensuring every piece is thoroughly coated in the delicious mixture. Let the pineapple marinate for at least 15-20 minutes at room temperature. This allows the flavors to penetrate the fruit. For an even deeper flavor, you can cover and refrigerate it for up to an hour.
5. Skewer the Pineapple: Once marinated, thread the pineapple chunks onto your soaked wooden or metal skewers. You can fit about 4-5 chunks per skewer, depending on their size. Leave a little space at the top and bottom of each skewer to make them easy to handle on the grill. Reserve any leftover glaze in the bowl for basting later.
6. Preheat and Clean the Grill: Preheat your outdoor grill or indoor grill pan to medium-high heat, around 375-450°F (190-230°C). It’s important that the grill is hot enough to create those beautiful sear marks quickly, which prevents the pineapple from getting mushy. Once hot, use a grill brush to clean the grates thoroughly. A clean grill is essential to prevent sticking. Lightly oil the grates with a high-smoke-point oil (like canola or vegetable oil) by wiping them with a folded paper towel dipped in oil, held with long tongs.
7. Grill the Skewers: Place the pineapple skewers directly on the hot, oiled grates. Grill for about 3-4 minutes per side. You are looking for deep, caramelized grill marks and for the pineapple to become tender and slightly translucent. As you turn the skewers, use a basting brush to apply some of the reserved glaze from the bowl onto the pineapple. This will add another layer of flavor and help create a sticky, glossy finish.
8. Serve Immediately: Once all sides of the pineapple are beautifully charred and caramelized, remove the skewers from the grill using tongs. Arrange them on a platter and serve them warm. Be careful, as the sugar glaze will be very hot!